(+)-Se-phenyl (4R,5S,6Z)-4,5-(isopropylidenedioxy)selenooct-6-enoate

Base Information

Chemical Name:(+)-Se-phenyl (4R,5S,6Z)-4,5-(isopropylidenedioxy)selenooct-6-enoate
CAS No.:140836-92-6
Molecular Formula:C₁₇H₂₂O₃Se
Molecular Weight:353.32
Hs Code.:

Synonyms:

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Chemical Property of (+)-Se-phenyl (4R,5S,6Z)-4,5-(isopropylidenedioxy)selenooct-6-enoate

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Technology Process of (+)-Se-phenyl (4R,5S,6Z)-4,5-(isopropylidenedioxy)selenooct-6-enoate

There total 8 articles about (+)-Se-phenyl (4R,5S,6Z)-4,5-(isopropylidenedioxy)selenooct-6-enoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 114364-60-2,114388-37-3,140836-85-7,140837-04-3
ethyl 3-((4R,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate

: 140836-92-6
(+)-Se-phenyl (4R,5S,6Z)-4,5-(isopropylidenedioxy)selenooct-6-enoate

Guidance literature:: Multi-step reaction with 5 steps

1: 91 percent / H₂ / 5percent Pd-C / ethanol / 2 h

2: 92 percent / PCC, NaOAc, molecular sieves 4 Angstroem / CH₂Cl₂ / 2.5 h / Ambient temperature

3: 1) BuLi / 1a) THF, -20 deg C to RT, 1b) RT, 2a) THF, -20 deg C, 2b) RT

4: 83 percent / aq. KOH / tetrahydrofuran; methanol / Ambient temperature

5: 1) NEt₃, 2) Bu₃P / 1) CH₂Cl₂, RT, 5 min, 2) THF, RT, 45 min

With potassium hydroxide; n-butyllithium; tributylphosphine; 4 A molecular sieve; hydrogen; sodium acetate; triethylamine; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane;

Reference yield:

: 213767-09-0
2,3-O-isopropylidene-L-erythrofuranose

: 140836-92-6
(+)-Se-phenyl (4R,5S,6Z)-4,5-(isopropylidenedioxy)selenooct-6-enoate

Guidance literature:: Multi-step reaction with 6 steps

1: 89 percent / PhCOOH / benzene / Heating

2: 91 percent / H₂ / Pd-C / ethanol

3: 93 percent / pyridinium chlorochromate (PCC), NaOAc, 4 Angstroem molecular sieves

4: 73 percent

5: 1) saponification, 2) formation of the triethylammonium salt

6: Bu₃P

With tributylphosphine; 4 A molecular sieve; hydrogen; sodium acetate; benzoic acid; pyridinium chlorochromate; palladium on activated charcoal; In ethanol; benzene;
DOI:10.1016/S0040-4039(00)91564-8

Reference yield:

: 114364-69-1,114364-70-4,146535-93-5,146535-98-0
ethyl <(3R,4S)-3,4-isopropylidenedioxytetrahydrofuran-2-yl>acetate

: 140836-92-6
(+)-Se-phenyl (4R,5S,6Z)-4,5-(isopropylidenedioxy)selenooct-6-enoate

Guidance literature:: Multi-step reaction with 5 steps

1: 36 percent / NaOEt, H₂ / 5percent Pd-C / ethanol / 168 h

2: 92 percent / PCC, NaOAc, molecular sieves 4 Angstroem / CH₂Cl₂ / 2.5 h / Ambient temperature

3: 1) BuLi / 1a) THF, -20 deg C to RT, 1b) RT, 2a) THF, -20 deg C, 2b) RT

4: 83 percent / aq. KOH / tetrahydrofuran; methanol / Ambient temperature

5: 1) NEt₃, 2) Bu₃P / 1) CH₂Cl₂, RT, 5 min, 2) THF, RT, 45 min

With potassium hydroxide; n-butyllithium; tributylphosphine; 4 A molecular sieve; hydrogen; sodium ethanolate; sodium acetate; triethylamine; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane;